Organic compound taking triazine and benzimidazole as cores and application thereof to OLED (Organic Light Emitting Diode)

A technology of organic compounds and benzimidazoles, applied in the field of organic compounds and their application in OLED, can solve the problems of complex production process, affecting the angular distribution of OLED radiation spectrum, etc., achieve high density, reduce the influence of deformation, high Tg temperature Effect

Inactive Publication Date: 2017-07-14
VALIANT CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The first two structures will affect the angular distribution of the radiation spectrum of the OLED. The third structure is complicated to manufacture, but t...

Method used

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  • Organic compound taking triazine and benzimidazole as cores and application thereof to OLED (Organic Light Emitting Diode)
  • Organic compound taking triazine and benzimidazole as cores and application thereof to OLED (Organic Light Emitting Diode)
  • Organic compound taking triazine and benzimidazole as cores and application thereof to OLED (Organic Light Emitting Diode)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Embodiment 1: the synthesis of intermediate I

[0050]

[0051] Under nitrogen atmosphere, weigh Ar 1 The bromide was dissolved in tetrahydrofuran (THF), and then bis(pinacolyl)diboron, (1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium(II) and potassium acetate were added, The mixture is stirred, and the mixed solution of the above reactants is heated to reflux at a reaction temperature of 70-90° C. for 5-10 hours; after the reaction is completed, water is added to cool, and the mixture is filtered and dried in a vacuum oven. The obtained residue was separated and purified by silica gel column to obtain Ar 1 pinacol borate;

[0052]

[0053] Under nitrogen atmosphere, the raw material 2,4,6-trichloro-1,3,5-triazine was weighed and dissolved in N,N-dimethylformamide, and then and palladium acetate, stir the mixture, then add aqueous potassium phosphate solution, heat the mixed solution of the above reactants to reflux at a reaction temperature of 120-150°...

Embodiment 2

[0066] Embodiment 2: intermediate Synthesis

[0067] When Ar 2 or Ar 3 When expressed as a structure of general formula (4),

[0068]

[0069] (1) In a 250mL three-necked flask, feed nitrogen, add 0.02mol raw material 2-bromo-benzimidazole, 0.03mol iodobenzene, 0.04mol sodium hydride, 0.004mol cuprous iodide and 0.01mol o-phenanthroline and dissolve in In 100ml 1,3-dimethyl-2-imidazolidinone, stir the reaction for 20-30h, after the reaction, add water and extract with dichloromethane, dry the organic layer with anhydrous sodium sulfate, and use petroleum ether and ethyl acetate The mixture was rinsed with eluent, the volume ratio of petroleum ether and ethyl acetate in the eluent was 1:100, and purified by column chromatography to obtain intermediate M;

[0070]

[0071] (2) Under a nitrogen atmosphere, weigh the intermediate M and dissolve it in tetrahydrofuran, and then dissolve the Br-Ar 2 -B(OH) 2 And tetrakis (triphenylphosphine) palladium is added, the mixtu...

Embodiment 3

[0104] Embodiment 3: the synthesis of compound 2:

[0105]

[0106] In a 250mL three-neck flask, blow nitrogen, add 0.01mol intermediate A1, 150ml DMF, 0.03mol intermediate B1, 0.0002mol palladium acetate, stir, and then add 0.02mol K 3 PO 4 The aqueous solution was heated to 150°C, refluxed for 24 hours, sampled and plated, and the reaction was complete. Cool naturally, extract with 200ml of dichloromethane, separate layers, dry the extract with anhydrous sodium sulfate, filter, rotate the filtrate, and purify through a silica gel column to obtain the target product with an HPLC purity of 99.3% and a yield of 75.4%.

[0107] Elemental analysis structure (molecular formula C 46 h 30 N 8 ): theoretical value C, 79.52; H, 4.35; N, 16.13; test value: C, 79.53; H, 4.33; N, 16.14. ESI-MS(m / z)(M + ): The theoretical value is 694.26, and the measured value is 694.57.

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Abstract

The invention relates to an organic compound taking triazine and benzimidazole as cores and application thereof to an OLED (Organic Light Emitting Diode) device. The compound provided by the invention has relatively high glass transition temperature and molecule thermal stability; the compound has low absorption and high refractive index in the field of visible light; after the compound is applied to a CPL (Circular Polarizing Filter) layer of an OLED device, the light extraction efficiency of the OLED device can be effectively improved; the compound also has a deep HOMO energy level and high electron mobility and can be used as a hole-blocking/electron transferring layer material of the OLED device; and the compound can be used for effectively stopping a hole or energy from being transmitted to one side of an electron layer from a light emitting layer, so that the compounding efficiency of the hole and electrons on the light emitting layer is improved, and furthermore, the luminous efficiency of the OLED device is improved and the service life of the OLED device is prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic compound with triazine and benzimidazole as the core and its application in OLED. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. The OLED light-emitting device is like a sandwich structure, including electrode material film layers and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. OLED light-emitting devices are current devices. When a voltage is applied to the electrodes at both ends, and the positive and negative...

Claims

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Application Information

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IPC IPC(8): C07D401/14C07D405/14C07D471/04H01L51/54
CPCC07D401/14C07D405/14C07D471/04H10K85/654H10K85/6572
Inventor 张兆超李崇
Owner VALIANT CO LTD
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